Boys Don't Cry (1999)

Based on actual events. Brandon Teena is the popular new guy in a tiny Nebraska town. He hangs out with the guys, drinking, cussing, and bumper surfing, and he charms the young women, who've never met a more sensitive and considerate young man. Life is good for Brandon, now that he's one of the guys and dating hometown beauty Lana; however, he's forgotten to mention one important detail. It's not that he's wanted in another town for GTA and other assorted crimes, but that Brandon Teena was actually born a woman named Teena Brandon. When his best friends make this discovery, Brandon's life is ripped apart.